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I reconnected with an old family friend a few months back. I was recently in town and he suggested we meet for dinner. The day prior to meeting up, he stopped by to say hey and confirm the plans (i.e. visual vetting). Five minutes before picking me up for the date, he texted “I’m bringing a 3rd person. Like to roll with multiple dates.” WTF! He showed up with an ex girlfriend of his who proceeded to ask me all kinds of personal questions over diner, like she was checking out her competition. She shouldn’t have worried because I was totally creeped out by the bizarre experience and he couldn’t have paid me to go out with him again.

After talking to this guy who was three years younger than me on an online dating site, he finally asked me for my number. I gave it to him and he sent me a text asking if I wanted to go on a date to see the moon rise at the beach. Corny, I know, but I had never been on a date like that so I agreed.

He called me the day of our date to ask me to meet him in the next town over for a cheap dinner before we headed out to the beach. Dinner was okay (we paid separately), and he was kind enough to make sure we ordered a vegetarian plate on my behalf since I’ve been a vegetarian for over a decade. After dinner, I asked if I could just ride with him to the beach since I wasn’t sure where it was and had never been to this town before. Hesitant, he told me that his car smelled like hot dogs, but he agreed to drive.

We got to the beach right in time, stayed for an hour or so and spent the majority of the time laughing. When I told him that I needed to head back (I had an event the next day, which he knew about), he just sat there starring at me like he was ready to kiss me. Awkward. Then when he dropped me off at my car, he walked me to my door, hugged me and kissed me twice on the lips like it was my forehead.

Later that evening he sent me a text saying that he “actually had a good time” like he was expecting the date to go horribly. I messaged him back to tell him that I had a good time as well but didn’t feel anything when he kissed me. He then informed me that he’s received similar “complaints” for girls in the past, so I asked him if he felt anything when he kissed me. He relied that he didn’t know what “anything” felt like. WTF?

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I had been dating this guy for almost two months and thought things were going well. We both liked the same kind of music, and got tickets to go to a rock concert. He was totally into me at the concert and on the way back to my house after the show. As we were snuggling on my loveseat, he wanted to have the “you and me” talk. He proceeded to tell me that he wasn’t “in love” with me (it hadn’t even been two months yet!) and that we should break up. In the beginning when we started dating, he said he wasn’t in a rush for anything serious, yet his excuse for ending things after almost two months was that he wasn’t in love with me. And to show interest in me during an amazing rock concert only to break up with me after, rude. The real kicker was that he wanted to stay friends and still do things together. I told him that would be too awkward, but he still continues to text me.

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A few years ago, a friend set me up with a guy who lived a few states away from me. We chatted on the phone a lot and when he was coming into NYC we agreed to spend the day together. We started with lunch and then wandered around, I was still feeling the situation out when we happened to pass by the Shakespeare in the Park box office and sure enough they still had tickets available. He suggested we get four tickets and I thought that meant he wanted to invite the friends who set us up (sweet but a bit awkward as this was still our first date). But that wasn’t the case. As we we’re walking away from the ticket booth, he asked if I’d mind if he invited someone else––another woman––with one of the extra tickets and I could use the fourth ticket for someone I knew.

I was a little suspicious at his hesitation and the way he phrased the request, so I pushed him further. Eventually he admitted that he had lined up a second date while he was in town, and he was supposed to meet her later in the day around the time the play started.

At first I was so taken aback I was actually ‘logical’ and polite about his request, eventually my sense returned and I realized he was using me to kill time till he could meet up with her. So I told him to loose my number.

Though the play was awesome.

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Red flags don’t wave louder than this … I actually found a copy of the book “How to Stop Getting Dumped” in my boyfriend’s room. When I casually prompted a “What’s this?”, I was met with a phony excuse that he was reading it “as a favor” to the author, who he’d claimed had given it to him (randomly?!). Needless to say, I knew I’d found myself a real winner. Clearly, either the book had terrible advice or the tidbits hadn’t been heeded. Worst boyfriend I ever had.

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After meeting a guy on an on-line dating site, we decided to meet for dinner that weekend. When I arrived, I was surprised he had a little girl with him (about 6 years old). He introduced his daughter, who he never mentioned to me or made any indication of having a child on his profile. He claimed it was his weekend with her and that’s why he brought her. I didn’t really know what to say. (Call me crazy, but I don’t think it’s appropriate for either sex to bring their child along when meeting a potential suitor for the first time.)

While we were deciding what to order, his daughter said she wanted to get a burrito and dad reminded her that she didn’t like the burrito last time, suggesting she should get the tacos instead. Well, the little girl started to throw a whiney fit, “But I want the burritoooooooo!” So that’s what she ordered.

And, of course, when the burrito arrived it wasn’t what she wanted. Instead, she wanted my tacos. I don’t really like burritos either and was really looking forward to the yummy fish tacos I ordered. I guess I gave my date some sort of look because he yelled, “Just give her the damn tacos!” What was I supposed to do? I had to give her mine and ask the waiter to bring another order of tacos while they ate. His daughter ate one taco and picked at the other one before deciding she didn’t like them either.

By the time my order arrived, they were both done eating and the daughter was ready to go. When the check came, my date asked for the second order of tacos to be on a separate bill for me to pay. He paid his portion and left me sitting there to finish my meal. The waiter seemed to understand my plight and told me the second order of tacos was on the house. Always a silver lining!

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On my second date with this guy I really liked, we went to a local bar near his house (I lived an hour away). We played pool, video bowling and in general had a good time. While he was playing pool with some guys, I chatted it up with one of their wives. Our conversation started out normally enough, but I quickly discovered she was kind of strange after saying a few things that made me uncomfortable. Well, her husband ended up leaving her at the bar and she claimed she was going to take a cab home. Instead, she immediately latched onto my date and I for entertainment.

When I told him I was ready to go, he asked me about inviting this woman (I’ll call her “R”) back to his house to play pool. I told him I was uncomfortable with that and just wanted to spend the rest of the evening getting to know him. We said our goodbyes and R said something about how she was also ready to go and, “I guess I better call a cab.” My date then invited her over to his house, suggesting she just call a cab from there. She accepted.

At his house, she kept going on and on about how much my date reminded her of her son (since she was more than twice his age), but kept touching him in a way that I thought was inappropriate, especially for someone who reminded her of her son. A couple of hours later, after I’d asked many times about calling her a cab, it seemed like she has no intention of leaving and he wasn’t pushing the issue. So I decide to drive myself home.

Well, my GPS wasn’t working fast enough, and since I was in the middle of nowhere, I decided to head toward “downtown,” thinking I’d have better luck picking up a satellite. After sitting in a grocery store parking lot for twenty minutes, I called my date hoping to get directions. He didn’t answer so I left a message saying I was lost and to please call me back. After maybe twenty more minutes and no return call from him, I felt like my only option was to go back to his house and use his computer to get directions. (There was nothing open at that time of night, and I had no where else to go.)

When I pulled into his driveway, I discovered the house was dark. I though one of two things must be going on: Either R finally left and he went to bed, or they were in bed together. I sucked it up and rang the doorbell. After ringing the bell twice, he answered the door. He immediately gave me a hug, claimed he was sleeping, and told me how happy he was that I came back. I figured that R had left, until he informed me that he was calling her a cab right then. She immerged from the bedroom shortly there after and told me, “Nothing happened! I mean nothing!” She grabbed her and headed back to the bedroom to presumably call a cab. A few minutes later she reappeared, screaming that she wasn’t going to take a cab home and that since my date was the one who brought her back to his house, it was his responsibility to get her home. When my date reminded her that it was always her intention to call a cab, she completely lost it. Looking me dead in the eye, she said, “He just had his hand up my pussy five minutes ago! What do you think about that?”

Then she launched at my “date” saying how they were fooling around and he just stopped as soon as I showed back up, and what kind of man does that to a woman? He tried to calm the situation down, but the chick was obviously very pissed off. So he called her a cab, which came shortly thereafter and she finally left. As soon as she was gone he tried to kiss me and I pushed him away. He tried telling me that nothing happened between them and but he didn’t deny her claims because he didn’t want to make a bad situation worse since R was acting crazy. He said they were just sleeping, so I asked why would he ask an absolute stranger that he just met—and was married by the way—to stay at his house and sleep in his bed? He didn’t have an answer.

Then I noticed that the clothes he was wearing that night were on the living room floor. I asked him why he had undressed in the living room, and he tried to tell me that that wasn’t what he had been wearing. Really? Are you kidding me? We spend the entire night together and I don’t know what he was wearing? I told him not contact me again, walked out the door and never looked back. Oddly my GPS decided to work right when I got back into my car: I wonder what forces were in play that night to make sure I found out early on what kind of man he really was.